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On Antifragility and why we need a National Entrepreneur Day

Antifragility. It’s an awkward word but one that sinks in to your consciousness as you read “Antifragile: Things That Gain from Disorder” by Nassim Nicholas Taleb. As a big fan of The Black Swan by the same author, I eagerly devoured this book. It takes the findings of the Black Swan and projects it outwards in to a philosophical and pragmatic outlook on modern life. Taleb is a divisive, opinionated, funny and passionate writer and this book, like his last, seems to have settled in to place at the base of my spine where I will carry it forever.

So what does antifragile mean? Well if you have a linear scale with “fragile” on the left, the common thought is that “robust” sits opposite to that on the far right. However what Taleb introduced with the notion of the Black Swan and expands upon now, is that robust doesn’t exist as this polar opposite state to fragility. Instead, a robust system is one that protects itself against known dangers, but as a consequence is hugely vulnerable to Black Swan, or unpredictable, events. Taleb instead proposes the notion of antifragility as it represents both preparation for known fragility whilst also allowing for the unknown. Whether they be small, large or Black Swan sized setbacks, the antifragile person or organization is set up to roll with the punches and still come out fighting.

If you work in an agile software development environment, or are an entrepreneur, or work in an entrepreneurial environment, then you are probably seeing some key familiarities with your daily work-life. The much discussed innovators burden is that they need to accept failure more than success, because every setback propels you forwards in the end, so long as you learn from your mistakes and can keep going. Failures should be bumps on the road to success, not big gaping pot-holes from which you will never emerge. Taleb himself sees this correlation between antifragility and start-up, Agile business culture, so I wanted to share some of his nuggets of wisdom.

On Entrepreneurs & Start-Ups

To answer the question of where Taleb sits on the scales of opinion regarding entrepreneurs, I present exhibit A:

My dream—the solution—is that we would have a National Entrepreneur Day, with the following message: Most of you will fail, disrespected, impoverished, but we are grateful for the risks you are taking and the sacrifices you are making for the sake of the economic growth of the planet and pulling others out of poverty. You are at the source of our antifragility. Our nation thanks you.

His impassioned view of entrepreneurs and scrappy start-ups ties very closely to his views on education. He believes in trial and error, and people who forge a path with nothing or little to lose and a lot to gain.

No one at present dares to state the obvious: growth in society may not come from raising the average the Asian way, but from increasing the number of people in the “tails,” that small, very small number of risk takers crazy enough to have ideas of their own, those endowed with that very rare ability called imagination, that rarer quality called courage, and who make things happen.

Also that start-ups fertilize the soil on which the economy will continue to grow:

The fragility of every startup is necessary for the economy to be antifragile, and that’s what makes, among other things, entrepreneurship work: the fragility of individual entrepreneurs and their necessarily high failure rate.

Whilst also forging the path towards greater knowledge:

Entrepreneurship is a risky and heroic activity, necessary for growth or even the mere survival of the economy. It is also necessarily collective on epistemological grounds—to facilitate the development of expertise.

So foster that pursuit of trying new things and learning from your mistakes and failures:

my characterization of a loser is someone who, after making a mistake, doesn’t introspect, doesn’t exploit it, feels embarrassed and defensive rather than enriched with a new piece of information, and tries to explain why he made the mistake rather than moving on. These types often consider themselves the “victims” of some large plot, a bad boss, or bad weather.

On Innovation

In turn, innovation evolves out of this entrepreneurial, trial and error, antifragile spirit:

How do you innovate? First, try to get in trouble. I mean serious, but not terminal, trouble. I hold—it is beyond speculation, rather a conviction—that innovation and sophistication spark from initial situations of necessity, in ways that go far beyond the satisfaction of such necessity (from the unintended side effects of, say, an initial invention or attempt at invention) … The excess energy released from overreaction to setbacks is what innovates!

Also an interesting outcome of the antifragile thinking is that the best ideas should come via negativa:

we know a lot more what is wrong than what is right, or, phrased according to the fragile/robust classification, negative knowledge (what is wrong, what does not work) is more robust to error than positive knowledge (what is right, what works). So knowledge grows by subtraction much more than by addition—given that what we know today might turn out to be wrong but what we know to be wrong cannot turn out to be right, at least not easily.

And just like a good writer or programmer who enjoys removing words and code to reach a more elegant solution, Taleb quotes one of my favorite Jobs-ism’s:

Finally, consider this … saying from Steve Jobs: “People think focus means saying yes to the thing you’ve got to focus on. But that’s not what it means at all. It means saying no to the hundred other good ideas that there are. You have to pick carefully. I’m actually as proud of the things we haven’t done as the things I have done. Innovation is saying no to 1,000 things.

On Risk Taking 

Risk taking is where the spirit of antifragility meets reality. There must be an acceptance of asymmetric payoffs:

To see why asymmetric payoffs like volatility, just consider that if you have less to lose than to gain, more upside than downside, then you like volatility (it will, on balance, bring benefits), and you are also antifragile.

As a product manager in software development, this quote rang so true about decisions our product team make daily:

In other words, if something is fragile, its risk of breaking makes anything you do to improve it or make it “efficient” inconsequential unless you first reduce that risk of breaking.

Taleb also proposes a heuristic against which to validate your ideas by using extremity of opinion, both positive and negative (of course):

consider this simple heuristic: your work and ideas, whether in politics, the arts, or other domains, are antifragile if, instead of having one hundred percent of the people finding your mission acceptable or mildly commendable, you are better off having a high percentage of people disliking you and your message (even intensely), combined with a low percentage of extremely loyal and enthusiastic supporters. Options like dispersion of outcomes and don’t care about the average too much.

It is also not about being right most of the time but instead being wrong with impunity and right that one time when it matters:

The frequency, i.e., how often someone is right is largely irrelevant in the real world, but alas, one needs to be a practitioner, not a talker, to figure it out. On paper, the frequency of being right matters, but only on paper—typically, fragile payoffs have little (sometimes no) upside, and antifragile payoffs have little downside. This means that one makes pennies to lose dollars in the fragile case; makes dollars to lose pennies in the antifragile one. So the antifragile can lose for a long time with impunity, so long as he happens to be right once; for the fragile, a single loss can be terminal.

On Education

Taleb is unforgiving in his assessment of the education system in the modern first world. The most powerful idea he presents is an assessment of the relationship of between education and wealth:

The implication is nontrivial. For if you think that education causes wealth, rather than being a result of wealth, or that intelligent actions and discoveries are the result of intelligent ideas, you will be in for a surprise. Let us see what kind of surprise.

I fully agree with this, now I read it, but I had never reviewed the relationship objectively in this way. Once you do, you see that entrepreneurialism and risk-taking in the US are the bases of future growth and wealth and it is this spirit that we should be fostering along with core STEM fields:

Many people keep deploring the low level of formal education in the United States (as defined by, say, math grades). Yet these fail to realize that the new comes from here and gets imitated elsewhere. And it is not thanks to universities, which obviously claim a lot more credit than their accomplishments warrant. Like Britain in the Industrial Revolution, America’s asset is, simply, risk taking and the use of optionality, this remarkable ability to engage in rational forms of trial and error, with no comparative shame in failing, starting again, and repeating failure.

And once again, what we see in software development so often now, is that some of the best developers are those passionate “amateurs” without the formal training:

Amateurs in any discipline are the best, if you can connect with them. Unlike dilettantes, career professionals are to knowledge what prostitutes are to love.

I just love that last line!

On Data

I found it very refreshing to read Taleb’s perspective on data, and particularly the dangers of big data. Working on the web you are constantly made-aware of the need to gather and use data to guide your decision-making. This is not something I disagree with per se, but something I am wary of, and Taleb captured my wariness in three words:

data increases intervention

Like a doctor who feels he must prescribe a pill in order to have a sense of agency in an uncertain situation, a product team will feel the need to constantly tinker with their product as a result of data, which is not bad in itself, but is compounded by the very quantity of data available:

In business and economic decision making, reliance on data causes severe side effects—data is now plentiful thanks to connectivity, and the proportion of spuriousness in the data increases as one gets more immersed in it. A very rarely discussed property of data: it is toxic in large quantities—even in moderate quantities.

So amid this large quantity of data, the real information can be lost, skewed or overlooked altogether:

Modernity provides too many variables (but too little data per variable), and the spurious relationships grow much, much faster than real information, as noise is convex and information is concave.

Going back to innovation via negativa, data should be used likewise:

Increasingly, data can only truly deliver via negativa–style knowledge—it can be effectively used to debunk, not confirm.

On Life

I will end with a more general quote, but one that demonstrates the underpinning of Taleb’s whole outlook and why this book just sang to me. The fact that life is about ups-and-downs. About failures and successes, and risks and rewards. To try and level everything out is to set yourself up for a bigger and more inevitable fall, like the economists who thought modern financial life had evolved beyond the boom-bust cycle just before the greatest depression in 60 years. There is no flat line through life, but if you are ready for the troughs and protected against the unknown, then the peaks will be all the sweeter and more lucrative:

The best way to verify that you are alive is by checking if you like variations. Remember that food would not have a taste if it weren’t for hunger; results are meaningless without effort, joy without sadness, convictions without uncertainty, and an ethical life isn’t so when stripped of personal risks


Managers as Curators

The dilemma of a fast growing company is one that needs little introduction. To grow is to add more of everything. More people. More projects. More customers. More money.

What is not clear to me is whether there must, and always will be, more layers. More hierarchy. More planning. More meetings. More stress.

Undoubtedly, to grow is to add complexity. If there are more moving parts then there more possible results from every action (and inaction). So much so that you cannot take all of them in to account with every decision, and some decisions will have unexpected outcomes. However some of these other items seem debatable. In fact, more than debatable. I think they naturally arise as a product of inertia rather than from any real management decision-making.

The core premise of Steven Johnson’s excellent “Future Perfect” book has been rattling around my head recently, which this quote nicely summarizes:

Increasingly, we are choosing another path, one predicated on the power of networks. Not digital networks, necessarily, but instead the more general sense of the word: webs of human collaboration and exchange

This quote broadly describes and accepts two fundamental points. Firstly that networks, not hierarchies, are the way to go. Secondly that the real intellectual horsepower in a company or any organization of people exists in the corners and at the edges of the network. The history of humanity is replete with examples of figureheads who drove through their vision despite the doubters, and so seeming to nullifying this second point. But I would counter that no person works in a bubble and there are no examples of these figureheads working alone. Always they are surrounded by a network or networks, small or large, that significantly help shape the vision. What the figurehead does is show great determination and foresight in seeing something through to the end. Either that or they are stubborn and lucky. The result is the same.

So what is being discussed here is not a suggestion we all pack up and move in to a small commune of common ideals, with no management and no leaders. I believe that strong or visionary managers and leaders can be a positive not negative force. Instead, I propose that we embrace the power of the networks as a management technique. By pushing sufficient power to the edges management can then act as a guide for the networks focus by defining the constraints within which the network operates. By constraints I mean defining what problems need to be solved and, most importantly, why. Networks are messy and noisy. Embracing it and letting the power of emergent and self-organizing behavior thrive is the opening chapter, but not the full story. It should be directed emergent behavior. How much direction is needed will be network specific, but leaders can be used to think at a broader level of abstraction than the more near-term parameters within which those in the trenches are normally restricted. Managers and leaders work to ground those problems and projects in a broader strategic context. Leadership in this sense doesn’t have to mean hierarchical oversight.

Importantly, there should not be just one big network either. There should be multiple overlapping networks, with all the hidden layers and complexity that comes with it. As Johnson says:

the power of the system comes not just from the individual peer networks, but from the way the different networks layer on top of one another.

So think of the managers and leaders as a network incorporated within lots of other networks that are self-organizing and collaborating around problems, topics, projects and interests. The information flow between the management network(s) and the others should be bi-directional. They need to feed equally off of one another. The managers must fold-in information from the internal networks as much as they do their own personal beliefs, opinions of other managers, actions by competitors and trends in the market.

This is how management changes from a job of hierarchical oversight in to that of being the teacher, the pupil, the scientist and the curator at the same time. The same statement applies in-fact to every member of all the networks. The only difference may be that their perspectives are either primarily tactical or strategic. The networks must be recursive in structure, meaning they are identical at all levels. Because I strongly believe that the Small can and must still exist within the Large.

So to reel this back in to the fast growing company issues, lets translate those initial problems using this idea of networks and managers as curators:

More people = More networks
More layers & hierarchy = Layers of networks not hierarchical oversight
More planning = Empowering the network to deliver what is best within strategic constraints
More meetings = More collaboration. If that means more meetings then fine.
More money = More money and more fulfillment from making that money

To lead in today’s societies or companies is not to construct a plan and get buy-in from below. Instead it is to be a scientist (think peer reviews and empirical evidence) and a curator. To promote network style collaboration and openly hypothesize to those networks on strategies, possibilities, scenarios and challenges. To then comb through the resulting cacophony of information for themes and threads that form the solid basis of what to do next and letting that inform what should be the next project to tackle.

This I believe can help enable companies to grow fast and grow happy.

Job titles are signposts

In the “Lets Make Mistakes” podcast, episode 50, there was a listener question that prompted a characteristic rant from Mike Monteiro. To paraphrase, the question was, “If you create wireframes, are you are designer?”, to which Mr. Monteiro became very heated in explaining that if you are helping to solve the problem at hand, then yes you are a “designer”, because you are designing solutions to problems. End of story.

I understand Monteiro’s line of argument very well, as it is something I have argued myself many times. He is adamant that no time should be spent on figuring out job titles. We should just unify in solving the problem. Makes perfect sense. I always hated being in an environment where a) there were titles next to names on office doors or cubicle badges and b) people aspired only to have their name next to that title instead of actually doing a good job. However I think there is a deeper point being missed here.

The phrase “to explain the problem is to start to solve the problem” immediately rang around my head as Mr. Monteiro picked up speed. The need to create job titles such as Information Architect, User Experience Designer and Content Strategist, is part of the process of understanding the problem. Roughly 5-7 years ago there was a burst of interest in Information Architecture. As websites grew, and the web matured, organizations realized that there was a mess of incongruent information on their web holdings, and no unified pattern of navigation. So, Library Sciences emerged from the physical bookshelves and started applying similar rigor to the web. Yes we gained a job title that may seem superfluous, but underlying this was a need to start thinking about the organization and navigation of information on the web in a more holistic fashion.

Looking back over the last 2-3 years there has been a similar surge in interest around Content Strategy. As the “content first” argument picked up traction, so a new specialist profession was born of people who do not manage content and it’s creation, but instead strategize around what that content should be, and to what broader organizational goal it should serve. Had people always been doing this job? Yes, absolutely. But was it common practice? Absolutely not. Hence a new job title and consulting business space was created to specifically serve and evangelize this need.

Now take User Experience (UX) and we see the same pattern. To again paraphrase Monteiro, “everyone is having a user experience, whether they are using the train or buying a coffee, so what the hell does a UX Specialist do?”. Well, as aggravating as the title may be, appending “UX” to a title is an implicit acknowledgement that the correct strategic dissemination and organization of information on your site is not enough for it to be successful. It is the physical embodiment of the realization that there is an emotional component to your website or application, and somebody needs to take responsibility for that.

If that person is called a “Designer” then great, just so long as there is someone or process to deliver on that, then who cares what they are called. Job titles in many way are signposts along the way to a better understanding of how to build and manage engaging websites and applications. They may represent a bureaucracy and hierarchy, and the many big business negativity that comes with that. But they can also represent the progression of understanding in the field.

Finding something to get behind

I just started a new job with Braintree as a Product Manager.

Thanks for reading!

Well, actually that is not all I wanted to say.  I have been mulling over what my work-life motivations were ever since deciding to look for a Product Manager job.  In my previous role I was a Project Manager / Business Analyst / QA / Engagement Manager for a small tech consultancy.  Basically I was the only non-dev on a project, and managed everything from client relationships and expectations, contracts and billing, through grasping and defining the requirements, testing and shipping the finished product.  It was a hands-on position that  really I enjoyed, and I learned a helluva lot.

As I approached the 2 year mark however, I felt an ever-growing need to pair the ownership and responsibility for projects I already had, with a broader sense of purpose and drive about why I was doing it.  I wanted to feel like I was contributing to more than a bottom-line of billable hours-per-client, which is what it always seemed to boil down to in consulting.  It’s not that we didn’t care about what we built for our clients, and when we were building them, they were our babies, but the hand-off at the end often resulted in a sadness for me, because I saw that as really only the beginning.  I wanted to dig in to analytics of usage, talk to users, and work to improve what we had built.  But often you were either not given the chance, or if you were, you may not agree with the direction being dictated by the client, you were just happy if you won the contract.

I decided to move to the product side, to find that broader purpose.  I wanted to find somewhere that would give me the responsibility and ownership I already had at the project level, and also give me a seat at the table for the broader, long-term strategic plan for the product or service as it evolves.  I wanted to join a team that was passionate, and cared about more than fulfilling hours obligations and satisfying the client, but instead constantly improving the product and delighting users or customers.  The difference between satisfying and delighting is crucial. However I had to tread carefully, and not walk from a great job in to a bad situation.

So I scouted out the Chicago landscape, and kept a close watch on the burgeoning start-up and tech scene.  The Built In Chicago site was a particular focus, but I also continued to attend the Agile Project Managers and Ruby meetups when I could, keeping my ear to the ground of who was doing good work, who was happy and who was not, and which products or services were making a splash.  Slowly, I constructed my list of target companies.  Looking back on which companies made that list, the one key component they all had was personality.  The characters of the people who worked there shone through on their website, or blog, or in job descriptions, and that was as, if not more, important than the product itself.  It indicated to me that the company saw the people who worked their as the primary asset, and my guess is that the people who worked there would in turn reciprocate this focus by caring about the product too which they were devoting their working life.

Braintree made the list early on.  Their team page was a good start, but they were active in the open source and Chicago tech community and the Founder, Bryan Johnson, was vocal about wanting to build a company that would be the best place he ever worked, as well as the best product in it’s sector. Fortunately I made the cut when they posted a Product Manager job, and I am just finishing week 3.  It is a wonderfully liberating place to work, that encourages freedom of expression, hard work and play, and passion for the cause.  Somehow, the payment gateway service doesn’t seem like a dry area of business at all, and to someone who is almost allergic to the word “finance”, that is a high compliment indeed.

I know I am in my honeymoon period, so feel free to take this 3 week assessment of my new awesome job with a pinch of salt.  But I think what is important, and something I took away from my last job and the whole process of deciding what to do next, is that I wanted to find something to get behind.  I don’t necessarily want strong leadership or management (however that obviously plays a part), but instead I want a clear purpose, a sense of personal control and freedom within boundaries, and the feeling of belonging to a cause.  Braintree is delivering so far, and long may it continue.  But regardless, I feel I have made an important personal decision about how I want to shape my working life, whether it be working for a company or running my own.

Some outside influences should be mentioned that helped me define this vision of my working life, so here is the list in case your interested:

Agile Project Tools Review

Over the course of the last 2 years, I have tried out a number of Agile project management tools.  These tools are very important to us as we are often on distributed teams, given we have an office in Mohali, India.  So although we follow an Agile approach to our custom dev projects, we cannot stick to the Agile commandment that all development and project resources should work in the same location . Therefore a simple and efficient Agile card board on the wall will not suffice.  We need a tool that can be referenced not only by the internal development teams in Chicago and Mohali, but also often by the client as well.  We emphasize an open and transparent approach to our client relationship, which means our clients can log in and see the progress whenever they wish. This includes joining the daily-stand ups if they want.

So here is a quick run through of the tools we have tried, and why we ended up settling onAgile Zen.

Note that this post was also cross-posted to the Triton-Tek website, you can see it here also:

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